Sometimes, there are servants who do get very attached to the master family. So much that their children follow in their footsteps and continue serving the family's descendants. Hence the reason why there are servants who come from a very long line of faithfully serving their masters.

Common in anime and manga, since 'servant families' were common in Feudal Japan - some of those relationships remain today, if only symbolically, and often pop up to be played for drama, action or romance. Their masters might also have some sort of particular affection for their servants (which the servants can return), leading to relationships such as Heterosexual Life-Partners (or, less common, Platonic Life Partners or Like Brother and Sister).

Examples:

Anime and Manga

Kaze no Stigma, where the first Arc is powered by the rebellion of a family of wind-ninjas who have been serving the Kannagi Clan for centuries, and have finally gotten tired of it.

Ouran High School Host Club: Mori is the son of a family that has served Honey-chan's family since the Warring States Era, and despite the relationship being officially dissolved, he continues to serve and protect Honey-chan with supreme loyalty.

Yu-Gi-Oh!: The Ishtar family has been serving the Pharaoh for thousands of years, most of that living in an underground labyrinth protecting his tomb. Resentment over this is a huge part of what fuels Marik's Start of Darkness.

In Fullmetal Alchemist, Ling's bodyguards Lan Fan and Fu come from a family that has served the Royal Family for a long time.

Subaru Konoe from Mayo Chiki! comes from such a line of butlers. The position is traditionally reserved for males, but Subaru has no brothers, and so Subaru has to jump through numerous hoops (most notably posing as a boy in public) to prove herself worthy.

Comics

The original story for Bruce Wayne's butler, Alfred Pennyworth, whose father, Jarvis, had been Thomas Wayne's butler. This particular version of Alfred was canon until Frank Miller's Batman: Year One, which established that Alfred had himself been Thomas Wayne's butler/valet, and had worked for the Wayne family since before Thomas and Martha Wayne were killed.

Doctor Strange's manservant Wong is from a family whose ancestor, Kan, pledged that the firstborn males of his family would be dedicated to the service of the Sorcerer Supreme.

Fan Works

The author of Top Dog creates one between the Hyuugas and the family of the Fourth Hokage in the Naruto branch; this immediately colors Hiashi Hyuuga's reaction to Naruto once he finds out his parentage.

In Progress, Princess Luna's maid Sundance is apparently descended from one of these. According to the side-story "Celestia vs. Time", Sundance's great-grandmother was a servant at the palace as well.

In Forrest Gump, Bubba's family has apparently been in service for at least a century. The montage which shows different generations serving seems to imply that they are serving different generations of the same family. In this case, it's treated as a bad thing, since their service originated during the time of slavery. This would be inverted when Forrest gave Bubba's mother what he felt was Bubba's share of his shrimp venture: she was now rich enough to afford a servant of her own.

Literature

The Butler family in Artemis Fowl has been serving the Fowl family for a long time (the earliest recorded relationship between the two families dates back to the Third Crusade). The first book posits the theory that this is actually where the word "butler" came from.

Afanasiy Zyukin from The Coronation is a butler in the third (I think) generation.

Thomas and Cyril Tanner come from a long line of people who've had a touch of the Sight, which is required for servants of the Nephilim. Needless to say, their family's been serving the Institute for a while.

Bridget Daly's family has served the Nephilim for generations.

Kitty Goes to Washington features a family that has served a female vampire for centuries. It turns out they are all descended from the two children she had before she became a vampire.

In the Liaden Universe, the family firm of dea'Gauss have served as attorneys to Clan Korval through many generations. One of the prequels reveals that it was a dea'Gauss who did the paperwork for the founding of the Clan, centuries ago, and Korval has had them on retainer ever since.

The Stewards of Gondor, sort of. Being a family tasked over to watch over the throne in absence of a king, they had been waiting for when the Rightful King Returns and should have recognized Aragorn as the rightful King of Men, but Denethor has other ideas.

The Brands of David Eddings' The Belgariad are hereditary servants to the Kings of Riva, serving as a sort of chancellor - handling the day-to-day drudge while the king makes the big decisions. So dedicated are they to their duty that upon assumign office, they abandon whatever name they had before, becoming known simply as 'Brand' (which was the name of the first one to hold the office). Similar to the Lord of the Rings example, they've spend a long time taking care of Riva and its throne while waiting for the return of the true king, but once he DOES show up, they never falter, and continue to serve faithfully. (With one notable, but quickly-corrected exception.)

The prequels mention Polgara's servants while she was Duchess of Erat (she technically still is, but in practice Erat is no longer a duchy and the house has been deserted).

Subverted in the Sharon Shinn short story "Bargain with the Wind" by way of another trope: My Grandson Myself. Nettie the Old Retainer housekeeper is actually an earth spirit who watches over the family. At the end of the story she recommends her "niece", Norah, as a replacement housekeeper, and then changes her form from an old woman into a young girl.

Honor Harrington: Although it's only in the first/second generation it seems likely that the Clinkscales and La Follet's will become this for the Harrington clan. In the case of the Clinkscales two generations have served her as Regent and Honor has actually formally adopted the clan as an extended part of the Harrington clan. In the case of the La Follets at least four members of the clan have served her in various positions (two male members as bodyguards and two female members as maids/advisors).

In David Eddings' The Elenium there are two parallel service legacies going on — the Sparhawk line has been hereditary champions of the monarchs of Elenia for several generations (it gets broken by Sparhawk marrying Queen Ehlana — he is still her champion as well as her prince-consort, but their daughter obviously can't serve as her own hereditary champion, and Ehlana will only have one child), while Kurik's family have been squires for the Sparhawks for several generations (this does not get broken — Kurik's son Khalad is squire for Sparhawk in The Tamuli, after Kurik's death in the last book of the Elenium).

A Blackadder always seems to end up with a Baldrick as a servant or something or other regardless of his status. What's interesting about this is that we actually see the bond being formed in the first episode, something we don't usually see in other examples of this trope.

On The Nanny, Niles' father was the butler for Maxwell Sheffield's family before Niles himself became Maxwell's butler.

Hudson, Rose and Mrs Bridges from Upstairs Downstairs all came from the Southwold Estate and serve the Bellamy family for more than thirty years without appearing to age at all. Other servants come and go - Ruby and Edward being pretty long-standing - but these three are rather immortal and look like they will outlive even Sir Richard...

Forgotten Realms has some long-runnners. Cormyrean court mages were direct descendants of the elven magess Alea Dahast and Baerauble Etharr, the first High Wizard of Cormyr from 26 DR, until Vangerdahast Aeiulvana retired in 1372 DR, followed by Caladnei — the first chief War Wizard supposedly not of this bloodline.

The Shiekah of The Legend of Zelda: Ocarina of Time has ever been faithful to the Royal Family of Hyrule, and has served them for generations as retainers, with Impa being the latest in a long line.

While not outright stated in The Legend of Zelda: The Wind Waker, a number of hints (in particular a portrait in Hyrule Castle of the pirates' near-identical ancestors serving as Princess Zelda's retainers) suggest that Tetra's pirate crew has been loyal to her family for quite some time.

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